Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 29, Pages 8471-8474Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201502215
Keywords
amino acids; asymmetric catalysis; imines; organocatalysis; phase-transfer catalysis
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Funding
- MEXT (Japan)
- Japan Society for the Promotion of Science for Young Scientists
- Grants-in-Aid for Scientific Research [26220803, 14J02264, 25708016] Funding Source: KAKEN
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The efficient construction of nitrogen-containing organic compounds is a major challenge in chemical synthesis. Imines are one of the most important classes of electrophiles for this transformation. However, both the available imines and applicable nucleophiles for them are quite limited given the existing preparative methods. Described herein are imine precursors which generate reactive imines with a wide variety of substituents under mild basic conditions. This approach enables the construction of various nitrogen-containing molecules which cannot be accessed by the traditional approach. The utility of the novel imine precursor was demonstrated in the asymmetric Mannich-type reaction under phase-transfer conditions.
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